


Wildest Dreams

by quirky_turtle



Category: Supernatural
Genre: Angst, Based on a Taylor Swift Song, Death, F/M, Fluff, I Made Myself Cry, Rating for one swear, Reader-Insert
Language: English
Status: Completed
Published: 2016-01-21
Updated: 2016-12-22
Packaged: 2018-05-15 08:18:45
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,313
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5778253
Author URL: https://archiveofourown.org/users/quirky_turtle/pseuds/quirky_turtle
Summary: <blockquote class="userstuff">
              <p>You and Dean fall for each other, but nothing lasts forever.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This is the first story I've posted on here. I was listening to "Wildest Dream" by Taylor Swift (I recommend listening to this song as you read this story), then this idea for a story popped into my head. I swear, a majority of the stories I write are fluffy. Just this one is kind of sad.

"Want to get out of here? Go to a bar?" Dean whispered in your ear.  
You looked up at him. Blood coating your hands. Tonight had been rough. You lost people. Your friends. You and your crew had met up with the Winchesters. Now, it was just you and them. They offered you a place at their bunker and now Dean was offering you a distraction.  
"I'm going to hell anyway." You shrugged and tried to smile back. Tonight was a night worth cashing in a five-year sobriety chip.

You got into the Impala. He drove for a while in silence. The town melted away as another one rose in the distance. You pressed your head against the window and closed your eyes.

Finally you two arrived at a bar. A new one, where no one knew you from Adam. You both grabbed a seat in the corner. After some drinks, you looked at the eldest Winchester. He was good-looking. Tall, handsome as hell. He had a bad boy look and act, but you could see through it.

After a few more drinks you leaned in.

~*~*~*~

"No one has to know. Just us. No labels." You whispered the next morning. You were both laying in your bed, naked. Your head was a little fuzzy, but you remembered last night's events.  
Dean looked over at you, threading his fingers through your hair, "Just us?"  
You nodded before leaning in slightly to kiss him on the lips.  
He pulled away just enough to ask, "So, this isn't a one-time thing?"  
"I don't want it to be." You murmured against his lips before reclaiming them.  
You could hear him whisper, "Thank god" against your lips before fully giving in to the kiss.  
You pulled away one last time, "Promise me something?"  
He looked at you, waiting for you to continue.  
"Promise you'll remember me and last night. No matter what happens to me, or us in the future." You looked into his eyes, hoping he would understand why this was important to you.  
"I promise." He nodded at you solemnly.

~*~*~*~

It had been over a year since you first slept with Dean. You loved him. You knew it and he knew it. But, you never talked about it. You never even dared to say the words out loud. You were a hunter. Love was dangerous. It could get you killed.

You and Dean were in the bunker, sitting at a table, sharing a bottle of Jack. The hunt had gone bad. Dean had been injured. If Cas hadn't shown up when he did, Dean would have died.

"Dean... we need to talk..." you set down your glass.  
"No we don't." He poured himself another.  
"You shouldn't have stepped in front of me like that! You were almost killed!" You glared at him.  
"I had to! Or else it would have been you. I had to protect you....Y/N...I need you." His anger quickly faded away, "I..."  
"Don't say it." You stopped him.  
"I fucking love you, okay!" He exploded then downed his Jack, "Why is that so bad?"  
"Because this can't last!" You stood up, "We don't get this kind of happiness. Something will ruin this."  
He stood up, towering over you. His voice was low and deep. It was familiar and almost soothing, "Nothing lasts forever. But this is good, now. Why can't we enjoy this now?"  
His eyes were almost pleading, you nearly melted, but not until you asked him this important favor.  
"If something happens to me, let me die. Don't make any deals. Promise me."  
His jaw clenched, not wanting to think about it, but you pressed on, "Keep living, just don't forget me. Okay? Remember that stupid date we went on to the lake. My sundress, my lipstick, anything. Just remember me."  
He nodded quickly and pulled you into his arms.

~*~*~*~

Blood poured out of your mouth. The blade stuck out of your chest. Cas couldn't save you this time. He was human. Dean was above you, begging you to stay with him.  
“Baby…why did you jump in front of me?” tears threatened to fall down his cheeks.  
“You know why.” you tried to smile, for his sake, but the pain was too much. Blackness began to ebb at the corners of your vision.  
“Please...stay with me. I need you… I love you, Y/N!” he gripped your hand tightly.  
You brought a hand up to his face, resting it gently of his cheek, “Promise?”  
His tears flowed freely as he nodded, turning his head to kiss your wrist.  
“I love you too, Dean.” your smile slowly fell. Everything faded away. The last thing you heard was Dean screaming your name.

~*~*~*~*~

Four months since they buried your body. Not many people showed up. It was really just Sam, Castiel, and Dean.

Dean sat on the edge of his bed. In one hand he held a bottle of Jack. In the other, a picture of the two of you together. He had kept his promise. He would not forget you. He brought the bottle to his lips, nearly finishing it. He didn't want to think. He wanted to get drunk. He was a man on a mission.

He felt your phantom hands on his shoulder. Your laughter rang in his ears. He finished the bottle quickly before dropping it to face “you”. Deep down inside, he knew it wasn't real. He knew this was pretend. But, having you in some form was better than the pain of knowing you were long gone.

So, every night he drank himself to oblivion. Just so he could see you. Even if it was just pretend. Even if it was just in his wildest dreams.

~*~*~*~*~

The End


	2. Chapter 2

**Summary for the Chapter:**

> Dean can't let you go. He asks Cas to check on you in Heaven, but Cas comes back with surprising news.

Dean had woken up to his normal hangover. He considered it part of his punishment for letting you down. He groaned as he sat up. He didn't bother to look at the empty half of his bed. It only filled him with disgust and regret. Aimed at himself of course. He pushed himself off the bed and headed towards the shower. 

He made good on his promise. No deals, no bringing you back. It helped him to know that you were at peace in heaven and weren't struggling here. You deserved better. He deserved worse.

Later that night, he sat at the table with Sam and Cas. Doing research.

“Cas…” Dean started, setting down his book. Castiel sighed and Sam looked over laptop.

“Dean, this isn't helping you.” 

Dean kept asking the angel to tell him about your heaven. What you saw and if you were happy. He reported back memories of the two of you. Your heaven was filled with Dean, Baby, and even Sam. 

“Please Cas…. Tomorrow’s her birthday.” Dean asked again, the pain evident in his eyes. 

Sam looked down. He knew these past few months had been hard on Dean. But he knew that you wouldn't want him to life like this. You wanted to be remembered, not obsessed over. 

Cas relented, as he always would, and disappeared. Dean’s shoulders relaxed some.

Cas came back, with a perplexed look on his face. 

“What is she seeing?” Dean asked.

“Um...nothing.” Cas looked down.

Any trace of happiness left Dean’s face, “What?”

“I couldn't find Y/N. Her soul… it's not there.”

Dean white-knuckled his bottle of whiskey. 

“She’s gone?” Sam asked, closing his laptop, “How does a soul just leave heaven?” 

“It doesn't. Not unless…” Castiel trailed off. 

“Unless?” Dean growled some.

Cas looked at Sam, searching for help.

“Unless she got pulled down to hell…” Sam finished hesitantly. Castiel shot him an apologetic look.

Dean was silent. Your soul was pulled down to hell. He slammed the whiskey onto the table, “Well, we’re going to go save her, right?”

“Dean… it’s not that easy…” Castiel started. 

“Bull shit. You’re saying that Sam and I can both come back from heaven, hell and god knows where else, multiple times, and we can’t save her once?” he stared at Cas with cold eyes. 

“We don’t know why or how.” Sam leaned forward on the table, looking up at his brother. These past few months had been hard on all of them. You had been a good friend to Sam, and having to watch his brother deteriorate only made matters worse. 

Dean picked up a book, “We figure it out.” 

Sam shot a look at Castiel, contemplating what to do. 

“Guys...it’s my fault she’s down there.” Dean eyes showed just how broken he felt inside. A rare occurance of him showing some of his feelings.

Sam sighed, “We’ll start researching. Tomorrow.” He finished before Dean would object, “It’s almost midnight. Try to get some sleep.” Sam stood up to leave the room. 

Dean looked to Castiel, “He is right, Dean. Rest.” And with those words, the angel was gone. 

A week passed with no answers. You haunted his nights.

**Notes for the Chapter:**

> So, the next two chapters are alternate endings. I couldn't decide between the two endings, so I decided to post both.


	3. 3A. Heaven

**Summary for the Chapter:**

> Alternate ending #1 where the reader was never sent to Hell.

You opened your eyes. You were in your room again, but it was dark. Usually, it’s morning. That’s when you were happiest. The few rainy mornings when you and Dean got to sleep in. No wonder why it was your heaven, 

But, this couldn’t be your heaven. You looked at the clock. It was 3am. The room was pitch black, except for the moonlight from the window. You could vaguely see Dean’s figure sitting on the edge of the bed. The glint of a bottle in his hand. 

This wasn’t heaven. Dean never looked this upset there.

You slowly walked across the room and Dean looked up and saw you. A bitter smirk on his lips. 

“Usually, I have to drink a hell of a lot more to see you. Must be the guilt.” he muttered the last part. 

You slowly wrapped your arms around him, his head against your stomach. You weren’t sure what was going on, but you kept quiet. 

“I’m sorry. I’m so fucking sorry, Y/N.” you heard him whisper into your stomach. 

You ran your fingers through his hair before tilting his chin up. Dean froze. Your touch wasn’t as ghostlike as it was before. It was… warm. He jumped away from you, standing on the other side of the bed. 

“What the hell?” he whispered again, this time his voice was harsh. 

“What’s wrong?” you asked, surprised by the crack in your voice. 

“This is just another nightmare…” he repeated to himself.

“Nightmare?” you asked and looked down at yourself. You were wearing the clothes from the night you died. Dried blood stained your shirt where you had had your guts ripped out. 

You looked up and saw Dean staring at you, he swallowed hard, “Here to remind me that I let you die? Go to hell? No need. I won’t forget.” you could hear the pain in his voice. Just like it sounded when you died. 

Your hand touched your stomach. You remembered the pain, but felt nothing else. Curious, you lifted your shirt some.

Dean looked away, “Don’t.” He didn’t want to see your wounds again. In the nightmares you always showed him and whispered to him how it was all his fault. He would watch the blood pour out of you as you told him you would never forgive him. 

You ignored him and looked. There was nothing there. Not even a scar.

“Dean…” you looked up at him, compelling him to look. 

Knowing he deserved every second, he gave in. You heard him gasp in shock when he saw no blood. He flipped on the lamp next to him, making you squint from the sudden brightness.

He kept looking at your stomach, at a loss for words. 

“Babe… I think I’m alive…” You tried to step around the bed to get closer to him, but he stepped back. 

“How?” his breathing was getting quicker, not sure how to process what he was seeing.

“I don’t know. Last thing I remember is lying in bed with you...well…” you trailed off and pointed upwards. 

“Cas said…” he shook his head, not caring anymore. He walked around the bed to meet you, “I don’t know if this is a dream, but if it is…” 

You cut him off with a kiss, filling it with all the passion and love you possibly could. He responded quickly, not wanting to waste a single second he had with you. 

After a few amorous hours, you lie in the bed together. You caressed his face as he stared at you. He grabbed your hand with his own and held it tightly.

With that you both feel asleep. 

~*~*~*~

You woke up the next morning, the sun shining in your window. You felt Dean’s arm tight around your waist. It was a little uncomfortable, but you knew he just wanted to reassure himself that you were actually there. 

You carefully turned in his arms to face him. You smiled as you saw his sleeping face. It almost looked peaceful. You brought a hand up to rest on his cheek. Sadly, that gentle touch was enough to wake him up. 

His eyes widened at the realization that you were still there. He opened his mouth to speak, but you gently kissed him, preventing that. 

“How long was I gone?” you murmured after pulling away, running your thumb over his knuckles.  

“Almost seven months.” he closed his eyes. 

“Seven months!” you nearly sat up in surprise, but his arms around you prevented you from doing so.

“How long did it feel like?” he asked after a few minutes of silence.

You thought for a few moments, “I'm not sure. It felt like eternity…but it was all one day. If that makes any-” you stopped talking when Dean hugged you tighter, burying his face in your neck.

“I’m so sorry. If I knew you were in Hell sooner…” you stopped him.

“Hell? I was never there, baby.” you shook your head to emphasize your point. 

“But Cas couldn't find you… it was a week ago.”

You looked him in the eyes, “Last thing I remember is you and me, in the backseat of Baby. I was in heaven, I swear.” 

He looked at you, trying to find any hint of you lying.

He gave up when he saw none, “How are you even back?” he whispered.

“Who cares? It's you and me. Just us.” you smiled up at him.

He mirrored your smile and repeated: “Just us.”

There were higher plans for the two of you. But you wouldn't find out exactly what those entailed for a long time.


	4. 3B. Hell

**Summary for the Chapter:**

> Alternate ending 2, where the reader was sent to Hell.

“Dean, I have something to tell you.” Cas announced, popping into the library as Dean and Sam were hard at work, researching bringing you back.

“Jesus, Cas!” Sam jumped, dropping the book he was holding.

“What is it?” Dean asked. His voice low. He had bags under his eyes from not being able to sleep at night. 

“I found an ancient spell. However, part of the text is illegible. I can’t promise that it will work, but-”

“It’s our best chance.” Dean finished, walking over to the angel, “What do we need?” 

Two hours later, the Winchester brothers had gathered all the needed ingredients. All but one. 

“Anything else, Cas?” Sam asked.

“One last thing. A mournful tear of a loved one.” he looked at Dean.

“I have to cry?” Dean asked. 

“A tear of true grief.” Castiel confirmed.

“Dean, cry?” Sam tried to joke, not sure how his brother would react. 

Dean picked up the bowl that Cas threw all the ingredients into and left the room. 

“Where is he going?” Cas asked Sam, who put up one finger. 

They heard the sound of a door slamming. In order for Dean to cry, he need to either get mad or get drunk first. He spent so much time concealing his emotions, that it was almost like he had to break a dam before he could let himself go. 

When they heard the sound of something breaking, Sam figured that Dean wanted to go with the anger route. 

After twenty minutes and at least thirteen broken objects later, Dean re-entered the library. His eyes were red, but there were no left over tears in them. 

“It’s done.” He handed Cas the bowl, “Now what?” 

Cas lit a match and blessed the flame. He dropped it into the mixture and the whole thing went up in flames, “We wait. When the flames dies, she should be back among the living.” 

The three boys sat around the burning bowl. Waiting. 

~*~*~*~

“Where is she?” Dean paced. The bowl was now just smoking. The flames had died a while ago. 

“Maybe it takes a little longer.” Sam tried to reason.

“No. The spell was clear. When the flames died, she should have been back.” Cas said, then realized his bluntness, “I am sorry, Dean.” 

Dean stood up and walked back to the table, “We keep looking.” 

They sat and continued to research silently.

~*~*~*~

Oxygen. Your brain screamed. Maybe this was your new punishment. This wooden box kept you trapped as your lungs burned. You kicked at the cover in frustration. Surprised by slight give of the wood, you tried again. You heard a slight creak. 

You continued to kick and punch at the wood, until it broke. Dirt started to fall in, but you pushed through it. Thankful for the slight wetness that made it easier to climb through. You clawed your way up, ignoring the pain on your knuckles. 

Finally, you feel nothing. Pull yourself up and you feel it. Oxygen returning to your lungs. You lay on the grass next to you and gasp in a few deep breaths, taking advantage of this while you can. You are sure that in 5 seconds you'll wind up back in the box.

You open your eyes and see that there are stars surrounding you. Hell usually didn't have stars. What if… what if this wasn't Hell? You had a thought and decided that it was worth a shot.

“Dear Castiel, please help me.” your voice sounded hoarse and barely scratchy. 

You heard a flap of wings and suddenly, Castiel was standing in front of you.

“Y/N?” he stared down at you, “The spell, we thought it didn't work.” he extended a hand to help you stand.

“S-spell?” you croaked out. 

When you got to your feet, you noticed that they didn't want to work for you, and you ended up falling into Castiel.

“Sorry!” your throat felt like the desert. 

Cas picked you up into his arms, “Worry not, you are safe now.” 

Next thing you knew, you were in the kitchen of the Bunker. Your eyes widened and Cas gently set you down in a chair.

“H-home?” 

He nodded and got you a water bottle from the fridge. You didn't know how much you were craving water until you downed the whole thing in one go. Cas handed you a second one and told you he would be right back. He disappeared. 

Less than a minute later he returned and flipped on the light switch. You flinched at the brightness that filled the room, but he didn't notice. You heard Sam’s voice, it was laced with sleep. What time is it?

“What is it Cas?” he walked in and saw you sitting there. Shock on his face. You looked down at yourself for the first time and grimaced. 

You were still wearing the clothes from the night you died. You saw the dried bloodstain on your shirt. Dirt caked on your skin and in your hair. 

“H-hey Sam.” you waved awkwardly.

He rushed over and hugged you, picking you up out of the chair. You couldn't help but smile and laugh at the younger Winchester. 

“What the hell Cas? Why did you need me to come to the kitchen?” you heard Dean’s voice coming closer. Sam let you down gently and stepped out of the way. 

Dean looked like shit. Bags under his eyes and he looked exhausted. But if you were honest, you didn't look any better. 

“Y/N?” he stuttered your name, looking at you in disbelief.

You ran over to him and hugged him tightly. His grip on you was instant and tight.

“I thought that the spell didn't work? Where was she?” Sam looked to Castiel. 

Dean pulled away just enough to look down at you, his arms never leaving you as realization crossed his face.

“She was where we left her.” he gently took your hand in his and looked at your blood knuckles, “She dug her way out.”

You looked down, suddenly a little self-conscious. Of course he would notice that. He had done the same thing years ago. 

Sam cursed, “Why didn't we think of that before hand.”

Castiel shook his head, “It was probably in the part of the text we couldn't make out.” 

“Hey, what matters is that I'm here.” you smiled weakly, trying to make them feel better.

Sam smiled back at you, “You should get cleaned up, then get some rest.” 

You nodded some and turned to go. You realized that Dean’s arm never left your waist as he walked with you.

~*~*~*~ 

When you reached the bathroom, Dean closed the toilet seat and silently gestured for you to sit on it. You obliged as he turned to the sink.

He knelt down before you, gently taking your hand. Using the warm washcloth, he carefully cleaned out the cuts and scrapes on your hand. His gentle touch was soothing. Almost lulling you-

“How long was it?” he asked gruffly. You instantly knew what he was talking about.

“A little over four years.” you quietly answered. It felt like you were in Hell for four years. In all actuality you knew it was nowhere near as long.

Dean's motions stopped as he looked up at your face, “That long?” 

You didn't reply.

Dean stood up and walked to the cabinet. He handed you a towel and muttered something about being back with clothes before leaving down the hall to your room. Well, his room. You did die, after all.

~*~*~*~

He kept your body wash, you noticed. It was still half full, like on the day you “left”. 

After scrubbing every inch of dirt and blood off of you, you stepped out of the shower and grabbed your towel. You quickly dried off and saw the clothes Dean left for you. You didn't even hear him come back in. You changed into a pair of your pajama bottoms and Dean’s old AC/DC shirt you had claimed a year back. Was it a year? How long were you dead for? 

You carefully walked down the hallway into the familiar room. You let out a slight sigh of relief when you saw Dean sitting on the bed. He stood up and took two strides to stand before you. He pulled you into his arms again, crushing you to his chest. 

You relaxed into his arms, wrapping your arms around his neck. Breathing in his familiar smell as he did the same for you. You wanted to stay in this moment, but you remembered your question. 

“How long since I died?” your voice was soft. 

“Seven months.” 

You nodded. Heaven had been different than Hell. Heaven was an endless Tuesday morning in bed with Dean. Time didn't exist. But when you were ripped out and dragged to Hell, every excruciating second was counted. Not that you would ever tell him that.

“I asked Cas to check on you about a week ago. It was your birthday. He couldn't find you. Y/N, as soon as we knew we started looking for a way to get you out, I swe-”

You cut him off with a soft kiss. It was sweet and chaste.

“Thank you.” you lightly touched his cheek.

He leaned into your touch, “I love you. I missed you so much.” he covered your hand with his own.

“I love you too.” you whispered reassuringly. You noticed how his shoulders relaxed slightly. 

You took his hand and crawled into your bed, exhausted by the night’s events. 

Dean slid in next to you and you saw him reach for the lamp on the nightstand.

“Wait… can we leave the lights on tonight?” you placed your hand on his arm to stop him.

He didn't need any explanations. He understood completely and nodded. 

He wrapped his arms around you again and settled in for the night. 

He fell asleep first. You scanned the room slowly. He hadn't changed the room at all. Your pictures were still there. Your dresser was still there. You closed your eyes and listened to Dean's slow and even breaths. You allowed yourself to fall asleep in his arms.

It wasn’t an easy night. You woke up screaming a few times, but Dean was always there. He knew how to help you through it, be it whispering in your ear that you were safe or just holding you to his chest as you cried silently. He had been there, and for much longer than you. He never showed any signs of annoyance or anger. Just love and acceptance. 

~*~*~*~

It was after your fourth nightmare that you refused to go back to sleep. What was the point if you just kept screaming? Dean however, knew how tired you were. 

He gently rubbed your back, knowing what it would do to you. 

You fought against the warm and heavy blanket of sleep.

Dean whispered in your ear, “Go to sleep.”

“Noooo.” you whined. Clearly exhausted.

“I’ll be right here.” you could tell by his voice that he was falling asleep as well.

You closed your eyes, slowly slipping. 

“I’m right here. I missed you, so much.” you heard him sigh softly.

You fell under. Sleep took over. Thankfully, the nightmares seemed to hide away. For that night at least. 

**Author's Note:**

> Please don't hate me. I'm trying to decide if I should continue this or let it end here. Thank you for reading my first story.
> 
> UPDATE: So, almost a year later, I decided to finish this story, with an alternate ending. Feel free to comment on which ending was your favorite.


End file.
